Thursday, May 31, 2007

Technologists think in black and white, zeros and ones, yes or no. But management is not all about yes or no. There is a grey area, let's call it the fuzzy bit. (For non-techs, a "bit" is the smallest unit of storage or calculation, and all other elements are comprised of bits. Each of the letters typed here are comprised of 8 or 16 bits, depending on which system you are viewing them from).

When I programmed on proprietary motherboards, we would occasionally come across a fuzzy bit, which oscillated between zero and one. As a programmer, the fuzzy bit caused all sorts of inexplicable errors in my code, but in management, it's an essential tool in the process of decision-making. Why? It promotes discussion and collaboration in reaching a final outcome, either one way or another. Technologists are not always comfortable with this, prefering a known, immediate outcome. But, an outcome squelchs discussion and exploration.

As a programmer, the fuzzy bit cost me countless lost days and all-nighters, and I dreaded encountering it. As a manager, I couldn't live without the fuzzy bit.

Wednesday, May 30, 2007

I am a prolific networker, it comes from my days as a consultant, where my network was my livelyhood. I've shunned the ways of consulting for life as a full-time CTO. But I still network.

Why network? It increases ones knowledge of technology. Don't know the latest Open source CMS tools, or how to scale MySQL, or optimal email backup stategies? Someone in my network knows, and would be happy to share.

I approach networking by doing the first favor. My good friend Kevin Sickles of Sun Microsystems put it best "plant the seeds, you never know where the flowers will grow". So I plant seeds. I don't track who's returned favors and who hasn't, that's not the point. It's having a whole network I can go to with a question when I am in need.

I've recently incorporated networking as I interview senior candidates. I look for past connections, and when a candidate is not a good fit for a position, but a good technologist, I might give them advice, and maintain a connection as they track into their next job. Just because they are not on my team, doesn't mean I can't learn from them, or even recommend them to another CTO. I recently found an excellent PM through a candidate I interviewed but never hired.

My tool of choice for networking is email (was doing this long before LinkedIn). For a connection email, I'll use subject "Ping", "Hey", or "Catchup", and simply ask how are things going. That way if the person is too busy to respond, they'll understand its just a touchpoint and we'll get another chance to connect. I also try to do 2 lunches a week with my network, nothing beats a face-to-face interaction. I roll through my contact list, ping some contacts, suggest lunch with others.

Friday, May 25, 2007

Technology is a service provider to its business at most companies, and its important to get feedback on that service. Its not always easy to do. Either the business doesn't want to tell you the bad stuff, or when they do, you and your team have a hard time hearing it.

I have a saying that helps frame this:- "Perception is Reality". If the business thinks we are providing bad service, then we are, regardless of what we might believe to be the facts. This is a lesson companies know to be true with consumers, yet IT organizations struggle, I believe because they are so enamored with the facts (mainly because we are engineers).

This saying also works in that it shifts focus from whether a team or individual is "wrong" or "bad", and moves focus to the type of service they are providing. A team can be good and provide bad service (and visa versa, although much less common IMO).

Thursday, May 24, 2007

I had lunch today with a programmer I hired and managed 14 years ago (another excellent LinkedIn outcome). Besides catching up and remembering the rest of the team, I got a view into the type of manager I was 14 years ago, and... I was awful!

Back then I focused on 3 things, technology, technology and technology. There was no "soft side" of management, at that time I thought management was telling people what to do. Luckily, they were a highly talented group of programmers, and as individuals they did some great stuff with the bleeding-edge, latest and greatest technology we were using (I also hadn't yet figured out risk of using new technlogy). But there was no "team", really. People helped each other out, but there was no break-through, what I describe as 1+1=3, when the team creates an outcome that no individual could have even conceived.

Wednesday, May 23, 2007

We have a great program in our technology department that I am quite proud of, called "Lunch AND Learn". We regularly have a team member give a subject-matter expert presentation on a technology topic to the rest of the team. Lunch is provided (pizza), and the goal is to provide a learning opportunity outside of one's normal job skills. The program is the brain-child of Gautam Guliani, our head architect.

We cover a wide variety of topics (the most recent was Word & Outlook Tips & Tricks, the next is Ruby on Rails). I once gave on overview on company executives and the products/departments they are responsible for. We also had one presentation on how to give a presentation, so team members would have the skills needed to present at a future Lunch AND Learn. We quite often have non-tech department staff join us.

The program was previously called "Brown Bags" where attendees brought their own lunch, but we upgraded the program since it was so successful. I can just see the proposal for next year, "Back massage AND learn" :-). Jokes aside, this is a program that will continue to have my full support.

Tuesday, May 22, 2007

Risk is something I never understood as a developer, optomistic is not a strong enough word to describe my approach. My favorite example was the day I independently decided our windowing system needed a complete rewrite (1988, pre Microsoft Windows 3.0). I announced to my boss that I would work through the night to get it down, and expect resolution in 24 hours. Well, two weeks later I had removed the last major bug (can someone say "whoops"?). If I had been managing by risk, this would have been approached completely differently (I.e. Peer design review, estimate assessment, plan B fail-over plan, business interruption consideration, and the list goes on...).

Managing by risk is asking the question "What could go wrong? What might not work as planned?", predicting that likelyhood, and planning mitigations and contigencies. I will often ask my team to include top 3 risks in project status reports as a mechanism to bring risks to the fore, and believe this to be a best practise. My experience has been that known risks can always be managed, and that unknown (or ignored) risks are the ones that cause grief.

Sharing a risk is itself a mitigation, and also serves the purpose of quantifying and qualifying it. (That idea alone would have saved me 20 all-nighters). Yes, I've ignored risks. Yes, I've had grief. But I've learnt my lesson enough to know that a focus on risk is a key to success.

Monday, May 21, 2007

I checked my Blackberry towards the end of dinner with an overseas colleague, and it was gently suggested this might be anti-social behavior. This sparked an interesting discussion, where I gave my usual pitch as to being more productive and available by checking email constantly. But its truly an interesting question.

Do human interactions need to be exclusive, or can I "double date", so to speak? I get a call from a colleague during a meeting that to can't take, so I email back "what's up?". I can get a request for tech help, and forward it without speaking to anyone, all while attending a kids soccer game or ordering a burger at a diner. I may be fooling myself, but I truly do believe I am more productive because of my Blackberry.

As to the answer to this question, in part this comes down to the expectation of social company. Baby boomer's single-task, and expect undivided attention. GenX/GenY grew up with IM, and accept multitasking.

If your kid looks up from a soccer game, and your typing on your Blackberry, will they say "Dad's multitasking" or not? However, I bet I'll be at more soccer games than the previous generation.

Friday, May 18, 2007

In corporate email systems, we have a reasonable set of tools for filtering most email spam, but why is all the rest of my email treated equal? My email comes in all different flavors, yet there is no tool to help distinguish that. It takes my own on-the-fly filtering to do that.

Setting up client-side rule-based filtering can wreak disaster when faulty rules hide critical emails (one case it was from an unhappy client who asumed they were being ignored). So I stay away.

The biggest issue for attempting to apply email filtering rules is context (ie what's important to the reader now). For instance, if one of my kids is sick, then every email from my family is of critical importance, otheriwse it goes into the "after work" queue.

Wednesday, May 16, 2007

LinkedIn reached critical mass about 6 months ago, and started to become a useful tool for me (I have 250+ contacts, resulting in a 1MM people network). Someone suggested the links in Google when you search a person was the difference maker. So far I've advertised jobs on my team, hired a programmer, tracked career changes and reconnected with colleagues I've not seen for 15 years. This is enough for me to deem it worth the effort to maintain. I also like that LinkedIn has made frequent changes, each making it easier to track changes in my network.

Just as many young people's online persona is their facebook or myspace page, my online persona is http://www.linkedin.com/in/jonwill - (you'll also find a link to my Myspace and Flickr pages there!)

I have a few simple rules for myself using LinkedIn:-1) Only connect with people I've met in person face-to-face2) No vendors unless relationship is stronger than just vendor (same for recruiters)3) No recommendations for people I currently work with

You'll notice not everyone follows this etiquette (nor is it official policy on linkedin), but it's easy enough not to respond to random invitations. If I know the person, I will give them my reason for not connecting.

Tuesday, May 15, 2007

The first 10 years of my career was spent working with newspapers and magazines, I've worked closely with journalists and editors (and publishers), and appreciate the work they do. To me, blogging is very different from journalism, but I'm not sure all agree.

Over dinner with Steve Fox, editor-in-chief of Infoworld (http://www.infoworld.com), he argued that many consumers don't make the distinction. He says many people believe journalists are "directed" by advertisers and publishers, as recently shown by the PC World magazine curfuffle. And since television is clearly directed by advertisers (look at product placement on American Idol, for instance), isn't journallism too?

I say no, journalism is an art that will persevere through media change. Blogging is simply opinion, a point of view. Consumers will seek out journalism, not peer blogging.

Or am I wrong, and is blogging the new "reality TV" of journalism? We'll find out soon enough.

Monday, May 14, 2007

(Note: This is not a tech posting) I taught myself to play guitar starting 5 years ago, and I am at the stage where I can learn to play most new songs I hear. Looking up chords on the internet is invaluable here, as is my iPod as I listen to these songs over and over again, pausing, rewinding, etc. I haven't tried lyrics on my iPod yet, I use my Blackberry for that.

Performing and reproducing music has given me a new appreciation for the music I listen to, both past and present. Which songs are simple 4 chords with powerful lyrics, which are complex or subtle, or out of the ordinary format (Beatles seems to have all of the above). It's also trial and error, which songs I "feel" and thus perform verses which songs just don't take when I try them on the guitar.

I've played at 6 open mics so far, and enjoyed them all. I've had my hits and misses, but I am really learning to appreciate the art of the performance of my fellow amateurs. Now when I go see a professional musician, they make it seem so effortless its just incredible, as so much goes into a performance.

While I am still a freshman when it comes to performing at open mics, I have some tips for newbies:-- Don't stop, pause, say "whoops". Noone knows when you make a mistake unless you tell them.- Stand-up. That's what the real performers do, and it really helps projection- Buy the cheapest mic, stand and amp on www.musiciansfriend.com and practise singing into microphone and playing amplified. Really helps with confidence- Record yourself (tape is fine, I use my Canon SD 600 digital camera), and play it back to hear what you sound like- Announce song writer and song name before performing each song (else everyone will think you wrote it)- Banter between first and second song. Connect with audience. "Is everyone having a good time" is an easy ice-breaker

I have to thank my friends at the Circle of Friends Coffeehouse in Pleasantville - http://www.songster.org - for allowing me to learn these lessons while playing to them. And I have a lot more to learn....

As I mentioned in my first ever post, the reason I've started blogging is that I can do it via email from my blackberry during my evening train commute home. This allows me to blog during work "down-time" and between evening emails.

So far, it's working well, with a few caveats:-1) No spellcheck2) No pasting URL links3) Writing a page-full4) BUG: Font occasionally switches to smaller font size

I will need to retest spellcheck for Blackberry, something I did 12 months ago but abandoned as unneccessary given my typically short emails. I have to type URL links out in full, leaving potential for error. And gauging what amounts to a page-full read is tricky, since Blackberry is different page size.

But besides these caveats, the process is working well. And a great way to close a work day.

I have been wanting to try Agile development for years, in fact I recently discovered this as a "goal" in my first 90 day deliverable in my current position. Being guided by a vendor, we now have our first foray in formal Agile development methodology, and the results so far have been above expectations.

The major benefits we've seen over waterfall methodology are (1) detailed daily progress (i.e. no surprises) (2) speed, and (3) quality. Our first project was a test-drive throw away, our next project will be put into production in a few months.

Thursday, May 10, 2007

I spent the day at the Tristate CIO Executive summit in NY. It was a great one-day conference, although the 7:30am start and jacket/tie dress code were not my style (I complied). It was an excellent networking event, I encountered fellow New York CTO club members who like myself were masquarading as CIOs. Event was put on by SIM (Society of Information Management), which I will now join.

The highlight of the day was a presentation titled "Inspiring culture, collaboration and change", by Colonel Curtis Carver of the US Army, West Point. Besides Curtis being completely inspirational himself, I was amazed to hear that every West Point cadet trains in technology, hands-on. They build circuit boards, write code, config networks, and build 3-tier applications. That's every cadet, every future leader in the Army! I guess they've decided technology is important. Imagine if your CEO, CFO and VP sales/marketing had all programmed while completing their degrees?

The Army is also a huge user of social networking technology, connecting every platoon leader around the world online, creating case studies, promoting discussions online, outside of the regular chain of command. There was a later session on social networking in corporations, by Tsvi Gal of Deutsch Bank (and fellow New York CTO club member) and IBM. This is a big topic that I am really getting excited about.

Wednesday, May 9, 2007

We started the New York CTO club (Igor Shindel and I) because we saw that many CTOs did not have a good network to get advice from. My contacts in Silicon Valley all seemed to have good networks, having worked with Joe at Apple, or Mary at Sun, and therefore having folks from which they could seek subject-matter advice. So, we wondered if we could create a network via a CTO club. The first few monthly meetings were lame, but then something clicked at a meeting called "Vendor Intelligence" where we discussed different vendors we used and how and why. We extended this meeting into "Vendor Intelligence II" at our next monthly meeting, everyone got very into it. My own breakthrough moment was getting information about a vendor from three CTOs who had recently signed contracts, right as I was myself in contract negotiations.

The club is coming up on it's 7th year anniversary. We've had some great speakers (including this morning's, Michael Miller, who was Editor-in-Chief of PC Magazine for nearly 15 years), but what really makes the club is the comraderie between the members. The New York CTO club works because it's a community of CTOs (or similar position) who help and argue with each other about technology and business. The advice is just spectacular, and cannot be beaten. It also helps that we have the same location and time for breakfast every month, we meet early so everyone can get to their jobs by 10am. We share a Yahoo Group for emails, although a number of conversations go off-line after inital connection. We are close to 70 members strong now.

I can safely say that I would not be half the CTO I am today without the experiences and advice I've gotten from the New York CTO club.

This is my inaugural first posting. I am clearly late to the game in the bloggersphere (spelling?), but what the heck, here I am. I am planning (hoping :-) to post blogs via my Blackberry during my daily home train commute. We'll see how it goes.

Disclaimer

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About Me

Jon started this blog as an opportunity to share his
technology management experience with a wider audience. Jon is technology advisor in NYC. Jon's past experience as a technology executive / CTO includes Experian CheetahMail, iVillage / NBC Universal, Kaplan, Grey Healthcare, Time Warner, Scholastic, Flat World Knowledge, Oxygen Media, News Corporation, CDnow, 24/7 Media and Bigfoot Interactive.
Jon was born in Australia, and moved permanently to the USA in 1986. In 2000, Jon co-founded the New York CTO Club, a non-profit professional organization, which provides a monthly forum for 80+ technology leaders from many of New York’s best-known companies to share strategies and ideas in a collaborative and collegial environment. Jon is also a mentor in Columbia University’s Executive Masters in Technology Management program, where he helps students present technology plans to business stakeholders. In 2008 he was named one of Infoworld’s top 25 CTOs.